Acetyl chloride → 2',4',6'-Triiodo-3'-ethyl-5'-acetyl-3-nitrobiphenyl-4-carboxylic acid

HRID 1976510Notes

Reaction equation

HRID 1976510 reaction equation
[I:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([I:10])[CH:5]=[C:4]([I:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:28][C:29](Cl)=[O:30]>>[I:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([I:10])[C:5]([C:29](=[O:30])[CH3:28])=[C:4]([I:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 223419932',4',6'-Triiodo-3'-ethyl-3-nitrobiphenyl-4-carboxylic acid

Product 1

HCID 223419922',4',6'-Triiodo-3'-ethyl-5'-acetyl-3-nitrobiphenyl-4-carboxylic acid

Procedure

Freidel-Crafts acylation is performed on 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13) in the presence of AlCl3 and CH3COCl to yield 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17). 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17) is then reacted with a zinc mercury amalgam and hydrochloric acid and heated to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18)

Sources & evidence

ORD record
ord-4b96bbcde4e044378351cb33e79d8368
Source dataset
uspto-grants-2001_05
Patent number
US06226352B1

Reaction notes

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